betadex and citronellal

In this work we used natural and modified cyclodextrins (β-CD and HP-β-CD) as encapsulating agents to improve citronellal properties. Using fluorimetric techniques, its aggregation behavior was studied for the first time. Its critical micellar concentration was seen to vary with the presence of cyclodextrins, which form 1:1 stoichiometry complexes with citronellal. The encapsulation constants and the scores obtained by Molecular Docking were correlated. Chromatographic (GC-MS) and sensory analysis confirmed that cyclodextrins improve the persistence of the aroma. Finally, the antimicrobial effect of citronellal against Escherichia coli and Bacillus subtilis in the presence and absence of cyclodextrins was studied. A combinatorial effect of citronellal, HP-β-cyclodextrin and Glucobay® as an antimicrobial mixture was observed. The results of this study not only demonstrated the potential of CD mixtures, but also that the growth caused by CD digestion may sometimes be greater that the antimicrobial effect of the agents used in this study.

Topics: 2-Hydroxypropyl-beta-cyclodextrin; Acyclic Monoterpenes; Aldehydes; Anti-Infective Agents; Bacillus subtilis; beta-Cyclodextrins; Cyclodextrins; Escherichia coli; Gas Chromatography-Mass Spectrometry; Hydrogen Bonding; Micelles; Molecular Docking Simulation; Nanotechnology; Oils, Volatile

Citronellal (CT) is a monoterpene with antinociceptive acute effect. β-Cyclodextrin (βCD) has enhanced the analgesic effect of various substances.. To evaluate the effect of CT both complexed in β-cyclodextrin (CT-βCD) and non-complexed, in a chronic muscle pain model (CMP) in mice.. The complex containing CT in βCD was obtained and characterized in the laboratory. The anti-hyperalgesic effect of CT and CT-βCD was evaluated in a pre-clinical in vivo study in a murine CMP.. The complex was characterized through differential scanning calorimetry, derivative thermogravimetry, moisture determination, infrared spectroscopy and scanning electron microscopy. Male Swiss mice were pre-treated with CT (50mg/kg, po), CT-βCD (50mg/kg, po), vehicle (isotonic saline, po) or standard drug (tramadol4 mg/kg, ip). 60 min after the treatment and then each 1h, the mechanic hyperalgesia was evaluated to obtain the time effect. In addition, the muscle strength using grip strength meter and hyperalgesia were also performed daily, for 7 days. We assessed by immunofluorescence for Fos protein on brains and spinal cords of mice. The involvement of the CT with the glutamatergic system was studied with molecular docking.. All characterization methods showed the CT-βCD complexation. CT-induced anti-hyperalgesic effect lasted until 6h (p <0.001) while CT-βCD lasted until 8h (p <0.001vs vehicle and p <0.001vs CT from the 6th h). CT-βCD reduced mechanical hyperalgesia on all days of treatment (p <0.05), without changing muscle strength. Periaqueductal gray (p <0.01) and rostroventromedular area (p <0.05) showed significant increase in the Fos protein expression while in the spinal cord, there was a reduction (p <0.001). CT showed favorable energy binding (-5.6 and -6.1) to GluR2-S1S2J protein based in the docking score function.. We can suggest that βCD improved the anti-hyperalgesic effect of CT, and that effect seems to involve the descending pain-inhibitory mechanisms, with a possible interaction of the glutamate receptors, which are considered as promising molecules for the management of chronic pain such as CMP.

Topics: Acyclic Monoterpenes; Aldehydes; Analgesics; Animals; beta-Cyclodextrins; Brain Chemistry; Chronic Pain; Cymbopogon; Hand Strength; Hyperalgesia; Male; Mice; Molecular Docking Simulation; Monoterpenes; Muscle Strength; Myalgia; Oils, Volatile; Spinal Cord